Alkali salts of fatty amino compounds



Patented Mar. 14, 1944 ALKALI SALTS OI FATTY AMINO COMPO UNDS Willard L.Morgan, Edgcwood, and Earle Davis McLeod, Rnmford, B. L, assig'norl toArnold, Hoflman & Co. Incorporated. a corporation of- Rhode Island NoDrawing. Application April 14, 1941,

Serial No. ssassa 14 Claims. (Cl. 260-4045) This invention relates tosalts of condensation products which are suitable as assistants for themodification of the properties of textile fibers, which assistantscannot be removed by washing or dry cleaning and which have nodeleterious effects on the fastness to light of colored fabrics.

Many materials have been used as textile assistants for altering thesoftness, the easy wetting or the repellency of textile fibers, but eachhas been subject to some fault, thustallows, oils or sulphonated tallowshave long been used in the fin ishing of textiles for softening effects,but these effects are not permanent and are lost the first t me thegoods are washed. These materials also suffer from rancldlty orobjectionable odor development in the goods. Fatty alcohols and simplealiphatic amides, which do not become rancid, have also been used astextile softeners, but these also wash out.

It is known that the quaternary salts of allphatic amides which areformed by the reaction of aliphatic amides with acids as well as similarfatty quatemaries produced from pyridines or the betaines and aliphaticimidazoles solubillzed as salts by treatment with acids are useful astextile modifying agents, and in particular as textile softeners,particularly as these materials alter or soften the fibers and cannotthereafter be washed off; In a similar way quaternary salts have beenformed from these various aliphatic amino bases by reaction ofsolubilizing acids, such as, acetic, hydrochloric, etc, and also bytreatment with alkylating agents such as diethyl sulphate, ethylchloride or chloroacetic acid. The quaternary salts of fatty acidcondensations with aliphatic polyamines have particularly been used forthese purposes.

As a consequence of the marked advantages secured with the aliphaticamino quaternaries on textiles, their use has been very extensive, butit has been found, unfortunately, when used on printed or colored cloththat all of these allphatic amino compounds have caused a very seriousalteration in the light fastness of the colored textiles. In the case ofcommercial colors or direct dyestuffs and the basic type dyestuffs theseeffects have been particularly severe and in many cases the resistanceto fading is reduced to pract cally nil. Direct dyestuffs are perhapsused more than any other dyestuffs in the cotton trades because of theirgeneral brightness and generally good resistance to light fading. Theserious reduction in light fastness arising with the various types ofaliphatic amino quaternary substances is also found with acid typedyestuffs which are the main type used on wool fabrics. Other types ofdyestuffs, such as rapidogens, in digosols and vats, as well as acetatecolors are affected in many cases although not universally as it appearsto be particularly true in the direct, basic and acid colors. Whilethere is some slight variation in the deleterious effects of the varioustypes of aliphatic amino quaternary substances on dyestuffs, none ofthese is in any way completely free of the difficulty and the use of anyof them on colored goods constitutes a considerable trade hazard and hasbeen the source of loss in the textile trade and unsatisfaction to theconsumer employing the goods because of a very poor light resistance. Asan example, a fabric dyed with Diphenyl Blue Green BL, direct dyestuff,E. I. du Pont de Nemours, which readily gives a 40-hour fading test inan ultraviolet fadeometer or resists a three months outdoorservicewithout any evidence of fading will after treatment in a solution orless of any of the aliphatic amino quaternaries described show evidenceof failure within a flve hour fading test, and at forty hours thedyestuff is almost completely faded out.

It is an object of this invention to provide a new class of textileassistants, such as wetting, washing, softening, lubricating andwater-proofing agents.

It is also an object of this invention to provide a new class of textileassistants, such as wetting,

washing, softening, lubricatin and waterproofing agents having improvedproperties and characterized by not having any deleterious fading effeeton colored textile materials.

As a further object of our invention, we describe new salts of aliphaticamino compounds useful as textile assistants which may be easily appliedfrom aqueous solutions to give finishes on cloth of a maximum softnessand which effects are completely resistant to washing and to drycleaning, and at the same time free of any deleterious effects upon thefading resistance of the dyestuffs employed on the colored cloth.

A still further object of our invention is to describe new salts ofaliphatic amino compounds which may be used to lubricate either yarns orfabrics so as to make the mechanical flow of these in weaving or sewingproceed smoothly.

We have found that the deleterious effects on fading of dyestuffs by theordinary aliphatic amino quaternary acid salts which have generally beendescribed as cationic active materials are due to their reaction withthe dyestufl and the formation of new dyestuffs of completely alteredand practically invariably decreased fading resistance to light. Newdyestufls are formed by reaction of the quaternary nitrogen acid saltswith dyestuffs carrying sulphonic acid groups, which is particularlytrue for most all direct dyestuffs and acid type dyestuffs. In thesedyestuffs the large color group carrying the sulphonic acid group formsa negative ion in water solution, and this negative ion reacts with thelarge positive substituted ammonium quaternary ion or cation formed fromthe quaternary compounds when they are dissolved in water. The cationcarries practically all of the organic compound attached to thepentavalent nitrogen, the entire group carrying a positive charge andonly'the acid radical coming from the solubilizing acid goes into thenegative ion formed, thus we may typify the reaction of the dyestuifwith a quaternary aliphatic amino acid salt by the following reactions,where D is the large organic dyestufl complex carrying the sulphonicacid group. The pentavalent nitrogen or quaternary compound is indicatedas car y three substituent organic radicals (R) and a hydrogen whichlatter arises from the solubilizing acid. The other radical, indicatedby A, hooked to the pentavalent nitrogen arises from the solubilizingacid which, for instance, may be acetic acid in which case A is anacetate radical.

D-SOzNli (DSOi)-+Na++ R R w R A n water a large negative ion. In thesecompounds nitrogen is only found in a trivalent condition and there areno pentavalent or quaternary nitrogens present. The new compounds whichwe propose to use as textile modifying agents and softening agents arefurther characterized by the presence of one or more groups of thefollowing types:

II II As will beseen these are amide and amidine groups, in which theacid hydrogen attached to the nitrogen has been replaced by an alkalibase indicated by ME, such as sodium or potassium. We have found that inaliphatic amide and aliphatic amldine compounds which carry therespective groups,

that the hydrogen is a weak acidic hydrogen which can readily bereplaced by the alkalies assaseo when these compounds are treated withstrong alkalies.

We may make our new alkali salts of aliphatic amides and amidines byreacting a wide range of aliphatic amide and amldine types of substanceswith strong alkalies. In general, the new softeners which-we describedare of the following general formula:

Y is used to represent either oxygen (=0) or an imide group (=NH) and tis a small whole integer being either 1 or 2. In the wide majority ofour compounds R1 corresponds preferably to a saturated aliphatic chaincontaining 6 or more carbons, or it may also represent other hydrocarbonradicals of 6 or more carbons, such as cyclo alkyls, an unsaturatedhydrocarbon, an aryl radical. or a residue from a terpene acid, and itmay carry other substituted groups such as hydroxyl, carboxyl, orchlorine. In each case the corresponding acid and acid chloride estersor nitriles may be used as a source to introduce this radical into ourcondensation products as will be shown later.

The alkali salts of the aliphatic amides are made by treating aliphaticamide products with strong alkalies. We may make our aliphatic amides,where t is equal to 1, by condensing suitable acids with thealkylolamines, amino acids, and polyamines. As suitable acids forcondensing to these products, we prefer those containing 6 or morecarbons and preferably saturated aliphatic acids, such as lauric,stearic, and palm oil acids, although we may use the unsaturated orsubstituted fatty acids such as ricinoleic, oleic, sebacic, orchlorostearlc; or the cycle aliphatic, aromatic, or resin acids may alsobe used, such as naphthenic, benzoic, creositinic, and abietic,

or the resin acid secured from rosin and maleic tions on the condensatessecured from aliphatic nitriles with amines, alkylolamines, amino acidsor polyamines.

The group X is of the nature depending entirely upon the type of amineused in the initial condensations with the fatty compounds, and X mustcarry hydroxyl, carboxyl, or amino groups. Thus the organic acids may becondensed with monoethanolamine in which case X is an ethanol group, andsimilar type compounds may be secured using other primary amino alkylolcompounds, such as, 2 amino, 2 ethyl, 1,3 propanediol; 2 amino, 2methyl, 1,3 propanediol; 2 amino 1 pentanol; 3 amino, 2 butanol; 2amino, 2 methyl, 1 propanol; and trimethanol amino methane. X may be amethylol group where aliphatic amides are reacted with formaldehyde. Inall these cases our alkali salts are made by treating the condensateswith strong alkalies. Where X carries a carboxyl group one convenientmethod of securing this is by condensing an amino acid with the otherorganic acid, and as suitable amino acids we may, use amino acetic acidor glutamic acid. Our alkali salts can readily be prepared also fromcompounds in which X carries free amino groups, such as may be securedby condensing the organic acids with any of the aliphatic polyamines orsubstituted polyamines, such as diethylene triamine; 'triethylenetetramine; tetraethylene pentamine; hexaethylene diamine; hydroxy ethylethylene diamine; ethyl ethylene diamine; 2,2 dlmethyl, 1,3 diamino ppane: 1,3 diamino isopropanol; beta,beta diamino diethyl ether; andbeta,beta, diamino diethyl thioether. In general we have found thatwhere we react aliphatic amines with fatty acids that the alkali saltsof the resulting aliphatic amide are not water soluble.

The new alkali salts of aliphatic amide and aliphatic amidine compoundsmay carry more than one of the characteristic respective groups:

P i ain t- .i 1 ME ME Such compounds, in which t is equal to 2, canreadily be made by reacting polyamines with more than one mol ohprganicacids. We may secure a similar condensate where t is equal to 2 byfurther condensing a polyamine organic acid condensate withformaldehyde.

The aliphatic amide and amidine condensations are readily carried out byheating the organic acids and amines at temperatures from 130 to 200 C.until the reaction is complete as shown by the loss of water. The moltenmaterials are then cooled down to below 100 C. and while still moltenare mixed with strong alkali solutions of caustic soda or potassiumhydroxide. Further water is then immediately stirred in in order tosecure soaplike pastes which can thereafter be diluted with furtherwater at the time these materials are to be applied to the textiles.

The formation of the alkali salts makes the basic organic compoundsoluble in water. The alkali salts of these compounds are found to showhigh substantivity to various textile fibers, such as cotton, viscose,cellulose acetate, rayon, jute, etc., and to give textile treatmentswhich are permanent to washing and dry cleaning. In general, while thelarger molecules are desirable for substantivity, they are also inclinedto be water insoluble, but by the formation of our alkali salts bytreating the original condensations with strong alkalies, we are able toincrease their solubility in water. In general we find the solubility inwater to also improve as the number of amino, carboxyl, and hydroxylgroups are increased and as the molecular weight of the fatty acid,etc., is decreased.

The aliphatic amide and amidine groups,

bases and weaker alkalies, such as ammonia or the various alkylol aminesand alkyl polyamides such, for instance, as monoethanolamine ordiethylene triamine.

these materials and form the corresponding am- In general, then we mayreplace the sodium or potassium hydroxide by monium and amine salts, butin general we prefer to use the" stronger sodium and potassiumhydroxide. As the aliphatic amino compounds are all very weak acids, thealkali salts of these compounds all show an alkaline reaction in watersolution. In some cases our alkali, salts of the aliphatic aminocompounds can be made by mixing with strong alkaline salts which providefree alkalies when dissolved in water. Examples of this type are soapsand the sodium salts of sulphonated alkylated biphenyl compounds.

It is apparent by reason of the large molecular weight of our aliphaticamino compounds that the actuaharnount of alkali needed to convert theseinto the alkali salts is a relatively small amount as will be apparentin the examples detailed hereafter. Our new alkali salts of aliphaticamino compounds possess marked emulsifying properties, and it ispossible to readily emulsify oils or waxes in pastes of these materials.These give very stable emulsions when diluted with water. In fact, wefind that our alkali salts will frequently emulsify considerablequantities of the aliphatic amino compound bases which have not beenconverted into the alkali salts, thus, making it possible to use lessthan molal quantities for the securing of apparently water soluble or atleast stable emulsions of these products. Manywater soluble compounds,such as, hydroscopic agents, for example, diethylene glycol, dextrose,or urea can, of course, be added directly to the water pastes of our newalkali salts where it is desirable to use these on textiles inconjunction with the new textile modifying agents.

As can be seen from the nature of our general formula, there are notpresent in any of our new substantive treating agents any pentavalent orquaternary nitrogens and it is apparent that our new alkali salts, whendissolved in water, ionize in a completely different way from thequaternary or cation active materials in that our products ionize into apositive alkali cation and a large organic ion which is'charged with anegative charge. Since the dyestufl' ionizes in a similar way, there isno tendency for negative ions of our textile treating agents to combinewith the negative ion of the dyestuif, and the nature of the originaldyestuif is completely preserved; thus, it is found that when our newsofteners and other textile modifying agents are put onto dyed clothirrespective whether the dyestuff used on the cloth is direct dyestuff,acid, vat, indigosol, rapidogen, or other types of dyestuff, theresistance to fading on exposure to light is found to be the same asthat exhibited by the untreated colored cloth.

In addition to many of our materials having a marked permanent softeningeffect on the textiles, we may apply many of these as lubricating agentsto yarns or textile constructions. or we may apply them to increase therewetting or absorbability of the cloth or conversely in some cases wemay apply them as waterproofing effects, all of which will be apparentin the examples hereafter described. Many of our compounds are alsouseful as detergents inasmuch as many of the products show distinctsoaplike characteristics in their physical natures and opcrate verysatisfactorily as cleaning agents for the washing of textiles and othermaterials.

The invent on will be further illustrated but is not limited by thefollowing examples in which the quantities are stated in parts byweight:

Esample 1 31.! parts (1 mol) of an aliphatic acid amide condensate offormula:

CnHu-Hl-NHCHrCHsOK was made by condensing equimolal quantities ofstearic acid and monoethanolamine at temperatures between 130' C. and200' C. To this condensate, at temperatures below 100 C., were added 3.5parts (1 mol) of 100% ammonium l vdroxide as a 28% ammonia solution andthe mix well stirred. Water was further added to this base to form acreamy paste of approximately 30% solids. This stock paste may then befurther diluted at the time of use to give solutions containing to 1%solids, and such solutions may be used to treat textile fiberswhereupon. after drying, the fabrics will be found to be softened andsomewhat water resistant. The softener is wash resistant and will notaifect the light fasteness of any dye which may be used on the cloth.

The water soluble ammonium salt of the aliphatic amino compound producedand used as a softener in this example is of the following IIcnHac-Nncmclhon was made by condensing equimolai quantities of lauricacid and monoethanolamlne between temperatures of 130 C. and 200 C. To24.3 parts (1 mol) of the above condensate, melted and at a temperaturebelow 100 C., were added 5.6 parts (1 moi) of solid potassium hydroxideas a 45% solution and the paste formed thorou hly stirred. The alkalisalt formed was further diluted with hot water to give a white paste ofapproximately 25% solids. This stock paste may then be further dilutedat the time of use to give solutions containing to 1% solids and suchsolutions may be used as softeners on textile yarns whereupon, afterdrying, the yarns w ll be found to be softened, that the softener washresistant, and that this softener will have no effect on the lightfastness of any dyes which may subsequently be used. Application of 1 toof the alkali salt by weight to the weight of the yarn supplies a verysatisfactory lubricating effect which facilitates the use of these yarnseither in knitting or spinning operations. The aqueous solutions of theabove compound show this material to be a good wettin agent for use ongreige goods and other'fabrics. In solutions of b to 1% it shows equallyas good washing properties on wool or cotton as is shown by ordinarysoaps.

The water soluble potassium salt of the aliphatic amino compoundproduced above is of the following formula:

0 CuHn-N-CHzCHrOH Example 3 I An aliphatic amino compound was. made bycondensing equimolal proportions of lauric acid and 2 amino, 2 methyl,1,3 propanediol at temperatures between 130 C. and 200' C. during whichtime the amide is formed. To 28.7 parts (1 moi) of the above meltedcompound and below C. were added 5.6 parts .(1 mol) of solid potassiumhydroxide as a 45% solution. This heavy base was thoroughly mixed andfurther dip luted with water to form a 30% solid paste. This stock pastemay further be diluted with water at the time of use to give solutionscontaining )6 to 1% solids which will impart a soft hand to yarns orfabrics. The softness thus obtained will be wash resistant, show no odordevelopment on aging, and in addition will not aifect the light fastnessof any dyestuff used.

The potassium salt of the above aliphatic amino compound used as asoftener in the above example is of the following formula:

Example I As another example of our alkali salts of allphatic ethanolamides, we first prepare an allphatic amide by condensing equimolalquantities of stearic acid and diethanolamine between temperatures of C.to 200 C. followed by the addition of 1 mol or more of diethanolaminecontinuing heating between 130 C. to 200 C. during which time the excessdiethanolamine reacts with the ethanol amide first formed and water issplit out. To 45.6 parts (1 mol) of this ethanol condensate is added 4.0parts (1 mol) of solid potassium hydroxide as a 50% solution. This heavypaste is thoroughly stirred and hot water added to give a 25% solidswhite paste. This stock paste may be further diluted, when desired, withwater to give solutions containing y; to 1% solids. 8olutions of thesestrengths. when used to soften yarns aid in further manipulations ofvyarns in weaving and sewing. The softening and lubricating effectproduced .on the yarns is wash resistant and when subsequently dyed willnot affect the light fastness ofthe dye used.

Example 5 An aliphatic amino condensate was made by floating equimolalproportions of rosin acid and tetraethylene pentamine at temperaturesbetween 130 C. and 200 C. The compound obtained was soft, semi-liquid'innature and dark amber. The rosin condensate obtained above may besolubilized with potassium oleate soap, as for example, 1' part byweight of the rosin compound may be added to 4 parts of a 50% potassiumoieate soap paste and the mixture thoroughly stirred at a temperature of60 C. to 80 C. during which time the rosin condensate will solubilizefrom the alkali obtained by the soap hydrolizing in aqueous solutions.This paste may be further diluted to give a white stock paste ofapproximately 30% solids. In use, this stock paste may be furtherdiluted with water to give solutions containing 1 to solids. Thesesolutions possess detergent properties as well as softening qualitiesand may be used in the washing and scouring of yarns or fibers therebyleaving the yarns in a softened, cleaned condition for finishing. Thesoftness imparted is resistant to washing and when further dyed willyield deeper shades with no effect on the light fastness of the dye thatis used.

The salt of the rosin amine condensate formed condensing equimolalproportions of ricinoleic acid and diethylene triamine at temperaturesbe- This base may be further diluted with hot water to give a whitepaste of approximately solids.

The sodium salt of the above condensate possesses tween 130 C. and 200C., duringwhich time the amide was formed and 1 mol of water split out.The compound obtained was liquid at room temperatures. 3 parts by weightof the ricinoleic condensate obtained, which is liquid at roomtemperatures, were added to 1 part of asodium salt of a sulphonated,allwlated, biphenyl compound, such as, the sodium salt ofdibutyl-ortho-hydroxylbiphenyl-disulfonic acid, dissolved as a 50%aqueous solution. The mixture was thoroughly stirred during which timethe ricinoleic condensate was solubilized by the alkali salt used. Thebase was further diluted with water to give a stock paste ofapproximately solids. In use, thispaste may be further diluted tosolutions containing lg to 1% solids which solution possesses goodwetting properties. Fabrics softened with these solutions re-wet easily,and by reason of this re-wettability the compound is applicable to"Sanforizing operations. In addition, any dyestufi which may be used onthe fabric is not affected in its light fastness by the softener used.

Example 7 370 parts (1 mol) of an aliphatic amino compound were made bycondensing equimolal portions of stearic acid and diethylene triamine attemperatures between 130 C. and 200 C. The amide formed was light yellowwith a melting point of 81 C. and possessed the following formula:

O CuHu--NHCHQCIBNH CHzGHaNH:

To 37.! parts (1 mol) of the above condensate were added 4.0 parts (1mol) of solid sodium hydroxide as a 50% solution. This base wasthoroughly stirred and hot water added to give a 30% stock paste. Thispaste may be further diluted in use, and in strengths of /2 to 1% solidsmay be used for softening fabrics. Fabrics thus softened with thesesolutions will possess very good drape and be resistant to washing. Noeflect will be found on the light fastness of any dyes which may havebeen used on the fabric.

The sodium salt of the above aliphatic amino condensate is of thefollowing formula:

0 cflnu-r l-r a-cmcnmncmonmn,

Example 8 As a further example of our alkali salts of aliphatic aminocompounds, we may first prepare a condensate of stearicacid and hydroxyethyl ethylene diamine by h a ing equimolal pr tions of the compoundsbetween 130 C. and 200 C. during which time the amide is formed and onemol of water is split out. \This condensate may be solubilized in waterbythe addition of strong alkalies as, for example, 37.8 parts (1 mol)may be solubllized by adding to the molten base at temperatures below100 C. 5.6 parts (1 mol) of solid potassium hydroxide as 9.45% solution.

emulsifying properties and, as such, may be used to emulsify waxes,oils, or the non-soluble condensate described above. For example, asmuch as 4 parts by weight of the aliphatic amino condensate obtainedabove may be melted and added to 1 part of the anhydrous potassium saltin the form of a 30% paste and the mixture thoroughly stirred attemperatures between 60 C. and 80 C. During this time the 4 parts ofbase will be emulsified by the alkali salt and the mixture may then befurther diluted with water to any desired concentration.

In use, the stock paste obtained may be further diluted with water tosolutions containing to 1% solids and thus used to impart softness toyarns or fabrics. Fabrics softened with this material possess a highdegree of softness which is resistant to washing, and no effect on theligh fastness of the dyestuif is obtained.

The alkali salt of the condensate obtained above, used as an emulsifierin this example,

, possesses the following formula:

. UnllasU-1TICH:CH:NHCHzCHzOH Example 9 An aliphatic amino condensatewas prepared by condensing 2 mols of stearic acid with one mol of 1,3diamino isoproponal at temperatures behard, light amber, and melted at80 C. to C.

To 64.1 parts (1 mol) of the molten condensate at temperatures between80 C. to C. were added 11.2 parts (2 mols) of solid potassium hydroxideas a 45% solution. The mix was thoroughly stirred and further dilutedwith hot water to yield a 25% light amber paste. This stock paste may befurther diluted by the addition of hot water to solutions containin H;to /2 of 1% solids at the time of use. When used in these strengths,this compound will impart a marked softness to various fabrics, such ascotton, viscose, cellulose acetate, linen, jute, etc., and the softnessthus obtained will be wash resistant and will have no effect on any dyesused on the fabric.

The potassium salt of the above condensate used in this example is ofthe following formula:

a still further example of our alkali salts of amino compounds may beprepared by first condensmg equimolal proportions of stearic acid andmula:

ll UnHuU-NHCHzCHaNHCHzCHzOH This condensate may be further condensedwith water is split out between secondary amino radicals and a compoundof the following formula is formed:

C "Ha-8 NHC HaOHr-N-C 11:0 H10}! 0 HI onnr -unomonr-ri-omcmon This waterinsoluble condensate may be solubilized by the addition of strongalkali, as, for example, 76.8 parts (1 mol) of the melted compound attemperatures between 80 C. and 100' C. were thoroughly stirred with 4.0parts (1 mol) of solid sodium hydroxide as a 50% solution. This alkalisalt possessin the formula:

0 CuHu--NHCHsCHr-N-CHsCHsOH 0 g l H: onmr- -i r-omom-N-omcmo'n may befurther diluted with hot water to 'give a white, creamy paste containingapproximately 35% solids. The above sodium salt, when used in a dyebeck,in the ratio of 6 pounds of this paste to 1200 gallons (200ths of 1%)imparts a soft hand to fabrics which is resistant to washing and agingand has no effect on the resistance of fading of any dyestuff whichmight be used.

Example 11 In preparing aliphatic amino condensates we may also condensean amino acid with a fatty acid as, for example, by condensing equimolalproportions of lauric acid and alpha amino isocaproic acid (leucine) attemperatures between 130 C. and 200 C. during which time 1 mol of wateris split out and a compound of the followwater solubility and the yellowpaste obtained may be further diluted to approximately 35% solids. Thestock paste thus made my be further diluted to concentrations of 1 to155% solids which solutions possess good wetting. foaming and detergentproperties.

Example 12 An aliphatic amidine condensate may be prepared by heatingequimolal proportions of lauric nitrile and diethylene triamine, duringwhich time the diethylene triamine and lauric nitrile form a compound ofthe following formula:

NH CuHn-b-NECHsCHsNHCHsCHsNH:

This compound may be solubiiized by treatment with strong alkali'as. forexample, 28.3 parts (1 mol) of the amidine condensate may be thoroughlymixed with 5.6 parts (1 mol) of solid potassium hydroxide as a 45%solution. The soluble alkali base obtained may be further diluted withwater to concentration of 40% solids. This stock paste. in use, may befurther diluted and as such used to impart softness to yarns or fabrics.The softness thus imparted is wash resistant, and the compound on theyarns or fabrics will have no eflect on the light fastness of any dyewhich may be used.

The alkali salts of the aliphatic amidine ob tained above has thefollowing formula:

As a further example of our alkali salts of poly amino condensates, wemay first prepare the condensate of lauric acid and ethylene diamine byheating equimolal proportions at temperatures of 130 C. to 200 C. Thecondensate thus obtained is light yellow, melting at 124 C., and becauseof its high melting point is difilcuitly soluble. This condensate may besolubilized by treatment with strong alkali as, for example, 24.2 parts(1 mol) of the lauric condensate may be treated with 4.0 parts (1 mol)of solid sodium hydroxide as a 50% solution. This base, when thoroughlystirred, may be further diluted with hot water and on continual stirringwill yield a smooth paste of apwith water to solutions containing 5. tol% solids proximately 30% solids. To 3 parts of this 30% solids paste isadded one part by weight of diethylene glycol and the mixture isthoroughly stirred at temperatures between 60 C. and C. This paste whenused in the ratio of 2 to 6 pounds per 50 gallons of water imparts tohard, twisted, acetate fabrics a soft handle which is resistant'towashing and gives a highly desirable drape. In addition there is noeffect on the light fastness of any dyestuif which might be used. Usedin the ratio of 4 to 6 pounds per 50 gallons this compound possesseswetting properties in aqueous solutions.

The alkali compound of the lauric condensate described above is of thefollowing formula:

0 CnHr-E-IiI-CHsCHsNHs As many apparently widely different embodimentsof this invention may be made without departing from the spirit andscope thereof, it is understood that we do not limit ourselves to thespecific embodiments thereof except as defined in the appended claims.

We claim:

1. A substituted amino compound of the following general formula:

0 I A a-tt-n-omomon in which Me represents an alkali metal and R: anorganic acid residue of more than 6 carbons.

3. A stearo ethanol amide having the following formula:

CuHu-k-N-CHzCHsOH in which Me is an alkali metal.

4. An organic amide of the following general formula:

0 Rr-&If-CHIOHINHCHQCHINH2 in which Me represents an alkali metal and R1an organic acid residue of more than 6 carbons.

5. A polyamino amide having the following formula:

O CnHu--III- CHzCHzNHCHzCHzNHI in which Me is an alkali metal.

6. An organic amide of the following general formula:

7. A polyamino amide having the following formula:

in which Me is an alkali metal.

8. A substituted amino compound of the following general formula:

in which Me represents an alkali metal, t is a small whole integer being1 or 2, and in which R1 represents a hydrocarbon radical of at least sixcarbon atoms and in which X is an alkyl group carrying a group selectedfrom the groups consisting of hydroxyl, carboxyl, and amino groups.

9. Aliphatic alkylol amides in which the acid hydrogen attached to theamide nitrogen is replaced by an alkali metal.

10. The process of forming an alkylol amide compound in which alkylolamides of an organic acid of over six carbon atoms are reacted with analkali metal hydroxide solution at a temperature below C.

11'. The process for forming an ethanol amide compound in which anorganic acid of over six carbon atoms is reacted with monoethanolamineat C. to 200 C. and thereafter reacted with an alkali metal hydroxidesolution.

12. Aliphatic polyamino amides in which the acid hydrogen attached tothe amide nitrogen is replaced by an alkali metal.

13. The process of forming aliphatic polyamino amide compounds in whichpolyamino amides of organic fatty acids of over six carbon atoms arereacted with an alkali metal hydroxide solution at temperatures below100 C.

14. The process of forming a polyamino amide.

compound in which an organic acid of over six carbon atoms is reactedwith diethylene triamine at 130 C. to 200 C. and thereafter reacted withan alkali metal hydroxide solution.

WILLARD L. MORGAN. EARLE DAVIS McLEOD.

